Syntheses of the l-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1

Poirot, Emmanuel; Zhang, Xiaodong; Whittaker, Noel F.; Kòváč, Pavol

doi:10.1016/s0008-6215(00)00265-2

Cited by 11 publications

(6 citation statements)

References 20 publications

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“…Peracetylated 3-(β-D-globotrihexosylthio)propionic acid was coupled to a polypropylenimine dendrimer core using O-(7-Azabenzotriazol-1-yl)-N,N,N’,N’,-tetramethyluronium hexafluorophosphate (HATU) and diisopropylethylamine to activate the carboxyl group (Poirot et al, 2001). In brief, an amount of derivatized dendrimer equal to 1.5 equivalents per terminal amine on the dendrimer core was resuspended in acetonitrile to which one equivalent each of HATU (Sigma-Aldrich) and diisopropylethylamine (Sigma-Aldrich) were added.…”

Section: Methodsmentioning

confidence: 99%

Multivalent dendrimeric compounds containing carbohydrates expressed on immune cells inhibit infection by primary isolates of HIV-1

et al. 2010

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Specific glycosphingolipids (GSL), found on the surface of target immune cells, are recognized as alternate cell surface receptors by the human immunodeficiency virus type 1 (HIV-1) external envelope glycoprotein. In this study, the globotriose and 3’-sialyllactose carbohydrate head groups found on two GSL were covalently attached to a dendrimer core to produce two types of unique multivalent carbohydrates (MVC). These MVC inhibited HIV-1 infection of T cell lines and primary peripheral blood mononuclear cells (PBMC) by T cell line-adapted viruses or primary isolates, with IC50s ranging from 0.1 – 7.4 µg/ml. Inhibition of Env-mediated membrane fusion by MVC was also observed using a dye-transfer assay. These carbohydrate compounds warrant further investigation as a potential new class of HIV-1 entry inhibitors. The data presented also shed light on the role of carbohydrate moieties in HIV-1 virus-host cell interactions.

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Section: Methodsmentioning

confidence: 99%

Multivalent dendrimeric compounds containing carbohydrates expressed on immune cells inhibit infection by primary isolates of HIV-1

et al. 2010

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“…The required compound 11 was obtained as follows. Crystalline (Poirot et al , 2001) diacetate 6 was treated (Saksena et al , 2005b) with methyl 6‐hydroxyhexanoate in the presence of boron trifluoride etherate and the 5‐(methoxycarbonylpentyl) glycoside 7 formed was deacetylated (→ 8 ). Reaction of 8 with thioglycoside 9 followed by deacetylation of the formed 10 gave 11 .…”

Section: Methodsmentioning

confidence: 99%

Immunogenicity of synthetic saccharide fragments ofVibrio choleraeO1 (Ogawa and Inaba) bound to Exotoxin A

Wade

Saksena

Shiloach

et al. 2006

FEMS Immunol Med Microbiol

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Recombinant exotoxin A (rEPA) from Pseudomonas aeruginosa conjugated to Vibrio cholerae O1 serotype-specific polysaccharides (mono-, di- and hexasaccharide) were immunogenic in mice. Monosaccharide conjugates boosted the humoral responses to the hexasaccharide conjugates. Prior exposure to purified Ogawa lipopolysaccharide (LPS) enabled contra-serotype hexasaccharide conjugates to boost the vibriocidal response, but Inaba LPS did not prime for an enhanced vibriocidal response by a contra-serotype conjugate. Prior exposure to the carrier, and priming B cells with the LPS of either serotype, resulted in enhanced vibriocidal titers if the Ogawa hexasaccharides were used, but a diminished response to the Inaba LPS. These studies demonstrate that the 'functional' B cell epitopes on the LPS differ from those of the neoglycoconjugates and that the order of immunization and the serotype of the boosting conjugate can influence the epitope specificity and function of the antisera.

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“…The synthesis and 1 H and 13 C NMR characterization of compounds 1 – 16 have been described earlier 4–8. In the case of compound 16 , its O ‐deuterated analogue 16d was prepared by dissolving 2 mg of the sample in three drops of CH 3 OD (Merck, Darmstadt, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…A satisfactory vaccine against cholera is not yet available. The synthetic monosaccharide and oligosaccharide derivatives5–8 are in the form of glycosides whose aglycons allow conjugation to proteins to mimic the fragments of the O ‐antigens of Ogawa and Inaba O ‐polysaccharides. The chemically synthesized materials are used as antigenic components of experimental neoglycoconjugate immunogens.…”

Section: Introductionmentioning

confidence: 99%

“…The chemically synthesized materials are used as antigenic components of experimental neoglycoconjugate immunogens. In previous studies,5–8 mass spectrometry has been used for molecular mass estimation following [M + NH 4 ] + ions in CI‐MS using ammonia as reaction gas. With the aim of finding proper methodology for structural elucidation of compounds of this type, we have used as a pilot part of a mass spectrometric study of the monomeric models (Scheme ) for EI‐MS.…”

Section: Introductionmentioning

confidence: 99%

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Electron ionization mass spectrometric study of monomeric models of O‐polysaccharides of Vibrio cholerae O:1, serotypes Ogawa and Inaba

et al. 2003

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Fragmentation mechanisms of electron ionization (EI) mass spectrometry of the title compounds have been elucidated by high-resolution (HR) mass spectrometric measurements of the elemental composition and measurements of the metastable transitions (B(2)/E, CID). The experimental results were interpreted with the help of Mass Frontier 3.0 software, which aided the elucidation of fragmentation mechanisms and helped to deduce structures of the ions formed. Characteristic under the conditions of EI-MS measurement was the production of protonated adducts. Three distinct pathways observed include the formation of oxonium type ions, the conjugated transfer of electrons in the pyranose ring, and cleavage of the acylamide side chains. By applying the results obtained, the molecular mass, as well as the structures of both the saccharide and acylamide side chain involved in related substances, can be determined.

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Syntheses of the l-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1

Cited by 11 publications

References 20 publications

Multivalent dendrimeric compounds containing carbohydrates expressed on immune cells inhibit infection by primary isolates of HIV-1

Multivalent dendrimeric compounds containing carbohydrates expressed on immune cells inhibit infection by primary isolates of HIV-1

Immunogenicity of synthetic saccharide fragments ofVibrio choleraeO1 (Ogawa and Inaba) bound to Exotoxin A

Electron ionization mass spectrometric study of monomeric models of O‐polysaccharides of Vibrio cholerae O:1, serotypes Ogawa and Inaba

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